Born January 20, 1958 in Clinton, South Carolina. Growing up the son of a career army officer, he led a nomadic life, attending ten different schools before graduating in 1976 from S. R. Butler High School in Huntsville, Alabama.

Served as editorial cartoonist for his college paper and managing editor of the alternative student newspaper while attending the University of North Alabama, where he graduated in 1980 with degrees in Art and History.

After working briefly as a staff artist for the Pittsburgh Post-Gazette and The Fayetteville (NC) Times, Bennett went on to serve as the editorial cartoonist for the St. Petersburg Times (1981-1994) and The Christian Science Monitor (1997-2007). He now draws five cartoons a week for the Chattanooga Times Free Press, having joined its staff in 2008.

Winner of The Pulitzer Prize for Editorial Cartooning in 2002, Bennett has earned almost every honor his profession has to offer. He's received the Sigma Delta Chi Award (2001), the National Journalism Award (2002), the National Cartoonist Society's Award for Editorial Cartoons (2002), the Robert F. Kennedy Journalism Award (2007), the John Fischetti Award twice (2001, 2005), the Overseas Press Club Award twice (2005, 2007), and the National Headliner Award three times(1999, 2000, 2004).

Past President of the Association of American Editorial Cartoonists, Bennett is the husband of artist Cindy Procious, and the father of Matt, Ben and Sarah.